Triethylamine → HCID 137328355, compound
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.CCN(CC)CC.[CH3:16][Si:17](Cl)([CH3:20])[CH2:18][CH3:19]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][CH2:19][CH2:18][SiH:17]([CH3:20])[CH3:16]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of 3-bromophenol (0.60 g, 3.47 mmol) in dry THF (15 mL) under nitrogen was added Et3N (0.48 mL, 3.47 mmol). A clear yellow solution formed immediately; after cooling to 0° C., dimethylethylsilyl chloride (0.43 g, 0.49 mL, 3.47 mmol) was added by syringe over a period of 10 minutes. The yellow color disappeared in 10 min, and a white cloudy solution formed. After 3 hr the thick reaction mixture was filtered, washed with 15 mL of hexane, and filtered again. Concentration gave a clear oil (quantitative weight recovery) that was used in the next step without any purification.
Workup
- customA clear yellow solution formed immediately
- customa white cloudy solution formed
- filtrationAfter 3 hr the thick reaction mixture was filtered
- washwashed with 15 mL of hexane
- filtrationfiltered again
- concentrationConcentration
- customgave a clear oil (quantitative weight recovery) that
- customwas used in the next step without any purification
Sources & evidence
- ORD record
- ord-60601e8ef4dc439b981fcc7cb2d00de1
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08618162B2
Reaction notes
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